Ammonium Chloride → 2-(1H-Pyrazol-1-YL)benzamide

HRID 397499Notes

Reaction equation

HRID 397499 reaction equation
[N:1]1([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8](O)=[O:9])[CH:5]=[CH:4][CH:3]=[N:2]1.[Cl-].[NH4+].Cl.C[N:19](C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[N:1]1([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([NH2:19])=[O:9])[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 47383832-Pyrazolylbenzoic acid

Product 1

HCID 218661722-(1H-Pyrazol-1-YL)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-pyrazol-1-yl-benzoic acid (50 mg, 0.26 mmol), ammonium chloride (28 mg, 0.52 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (100 mg, 0.52 mmol), 1-hydroxy-7-azabenzotriazole (71 mg, 0.52 mmol) and diisopropylethylamine (0.17 ml, 1.0 mmol) in N,N-dimethylformamide (0.75 ml) was stirred at room temperature for 5 h. Water was added and the reaction mixture was extracted with ethyl acetate. Drying and solvent evaporation gave 2-pyrazol-1-yl-benzamide; 1H NMR (CD3OD, 400 MHz) δ7.92 (d, 1H, J=2.4 Hz), 7.70-7.48 (m, 5H), 6.49 (m, 1H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customDrying
  3. customsolvent evaporation

Sources & evidence

ORD record
ord-30b12dc29c5e4b649b03c920649f2eaf
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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